Potassium Fluoride → N-[(1RS,2RS)-3-(4-chlorophenyl)-1-methyl-2-{4-(3-thienyl)phenyl}propyl]phthalimide

HRID 376184ノート

反応式

HRID 376184 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH:9]([N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])[CH3:10])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:35]1[CH:39]=[CH:38][S:37][CH:36]=1)CCC.[F-].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([C:35]3[CH:39]=[CH:38][S:37][CH:36]=3)=[CH:3][CH:4]=2)[CH:9]([N:11]2[C:12](=[O:21])[C:13]3=[CH:20][CH:19]=[CH:18][CH:17]=[C:14]3[C:15]2=[O:16])[CH3:10])=[CH:24][CH:25]=1

参加物

6

反応物 3

HCID 522689Potassium FluorideHCID 10959689Stannane, tributyl-3-thienyl-HCID 19073589N-{(1RS,2RS)-2-(4-bromophenyl)-3-(4-chlorophenyl)-1-methylpropyl}phthalimide

生成物 1

HCID 19073667N-[(1RS,2RS)-3-(4-chlorophenyl)-1-methyl-2-{4-(3-thienyl)phenyl}propyl]phthalimide収率 72.9%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

113 mg of N-{(1RS, 2RS)-2-(4-bromophenyl)-3-(4-chlorophenyl)-1-methylpropyl}phthalimide prepared in the same manner as in Example 114, was dissolved in 3 ml of toluene, and 99 mg of tributyl(3-thienyl)tin and 14 mg of tetrakis(triphenylphosphine)palladium (0) were added thereto. The mixture was refluxed under heating for 3 hours in a light-shielding nitrogen atmosphere. The reaction solution was left to cool to room temperature. Then, 2 ml of a 5% potassium fluoride aqueous solution was added thereto, and the mixture was stirred for 30 minutes. Insoluble matters were separated by filtration. Then, ethyl acetate and water were added to the filtrate for liquid separation. The organic layer was collected by separation, washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=100/1→30/1) to obtain 83 mg of N-[(1RS, 2RS)-3-(4-chlorophenyl)-1-methyl-2-{4-(3-thienyl)phenyl}propyl]phthalimide

後処理

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 3 hours in a light-shielding nitrogen atmosphere
  3. waitThe reaction solution was left
  4. customInsoluble matters were separated by filtration
  5. additionThen, ethyl acetate and water were added to the filtrate for liquid separation
  6. customThe organic layer was collected by separation
  7. washwashed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe drying agent was separated by filtration
  10. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-89b8b33818b642c7bd0d3d1805de4067
出典データセット
uspto-grants-1996_01
特許番号
US05488149

反応ノート

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